Hydrazine hydrate (1:1) → 3-(2,2,3,3,3-Pentafluoropropoxy)methyl-4-methylaniline

HRID 373362Notes

Reaction equation

HRID 373362 reaction equation
[F:1][C:2]([F:20])([C:16]([F:19])([F:18])[F:17])[CH2:3][O:4][CH2:5][C:6]1[CH:7]=[C:8]([N+:13]([O-])=O)[CH:9]=[CH:10][C:11]=1[CH3:12].O.NN>C(O)C.[Pd]>[F:1][C:2]([F:20])([C:16]([F:17])([F:19])[F:18])[CH2:3][O:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:9]=[CH:10][C:11]=1[CH3:12])[NH2:13]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 150701683-(2,2,3,3,3-Pentafluoropropoxy)methyl-4-methyl-1-nitrobenzene

Product 1

HCID 150701693-(2,2,3,3,3-Pentafluoropropoxy)methyl-4-methylanilineYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In 40 ml of ethanol, 7.30 g (0.0244 mol) of the nitro compound obtained in Example 1 was dissolved. The solution was added with 0.1 g of 10% Pd-C and 3.66 g (0.073 mol) of hydrazine hydrate and refluxed on a hot water bath for one hour. After allowed to cool by itself, the solution was passed through a Celite layer to filter out the catalyst and then washed with ethanol. The filtrate was concentrated, dissolved in dichloromethane, washed with water, a saturated sodium bicarbonate aqueous solution and a saturated sodium chloride aqueous solution, and dried over anhydrous potassium carbonate. The solvents were distilled off and the residue was fractionally distilled, collecting the fraction having a boiling point of 82°-83° C. at 0.18 mmHg. There was obtained 6.09 g of 3-(2,2,3,3,3-pentafluoropropoxy)methyl-4-methylaniline in a 93% yield.

Workup

  1. temperaturerefluxed on a hot water bath for one hour
  2. temperatureto cool by itself
  3. filtrationto filter out the catalyst
  4. washwashed with ethanol
  5. concentrationThe filtrate was concentrated
  6. dissolutiondissolved in dichloromethane
  7. washwashed with water
  8. dry with materiala saturated sodium bicarbonate aqueous solution and a saturated sodium chloride aqueous solution, and dried over anhydrous potassium carbonate
  9. distillationThe solvents were distilled off
  10. distillationthe residue was fractionally distilled
  11. customcollecting the fraction

Sources & evidence

ORD record
ord-499f6b543fd34cbf8d4a283826eec452
Source dataset
uspto-grants-1992_11
Patent number
US05162583

Reaction notes

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